Thiazole → Dicyclopropyl(1,3-thiazol-2-yl)methanol

HRID 410531

Reaktionsgleichung

C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH:11]1([C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH2:13][CH2:12]1>C1COCC1>[CH:11]1([C:14]([CH:16]2[CH2:18][CH2:17]2)([C:7]2[S:6][CH:10]=[CH:9][N:8]=2)[OH:15])[CH2:13][CH2:12]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

n-Butyllithium (2.5 M in hexanes, 0.953 mL, 2.38 mmol) was added to a stirred, cooled −78° C. mixture of thiazole (0.169 mL, 2.383 mmol) in THF (5.0 mL) and the mixture was stirred at −78° C. for 15 min. A solution of the dicyclopropylmethanone (250 mg, 2.27 mmol) in THF (3.0 mL) was added dropwise and the mixture was stirred 30 min at −78° C. and then the temperature was allowed to reach room temperature. The reaction was quenched by addition of water and the mixture was extracted with ethyl acetate (3×). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give dicyclopropyl(1,3-thiazol-2-yl)methanol (412 mg, 2.110 mmol, 93% yield). MS APCI: [M-OH]+ m/z 179.0.

Aufarbeitung

stirringthe mixture was stirred 30 min at −78° C.
customto reach room temperature
customThe reaction was quenched by addition of water
extractionthe mixture was extracted with ethyl acetate (3×)
washThe combined organic fractions were washed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvent was evaporated under reduced pressure
customThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-0581596923da4abeb91e5e0af4170c6e
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08759366B2

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